organic nomenclature 2010

7/23/2019 Organic Nomenclature 2010

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O R G A N I C C H E M I S T R Y

Nomenclature

Of

Organic CompoundsMSAESMALLA

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form the chemical basis of life

more abundant than inorganic compounds

Organic Compounds


obtained from plants and animalscomposed mainly of carbon and limited

number of other elements

most contain more atoms and havemore complex structures

covalently bonded

nearly all are insoluble in water

are non-electrolyte

have low melting point and boiling point

derived from mineralscompositions are quite varied and include

most of the elements

contain relatively few atoms and havesimpler structure

ionic bonded

many are soluble in water

are electrolytes

have high melting point and boiling point

Organic compounds Inorganic compounds

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Organic Compounds


Hydrocarbon

Aliphatic Aromatic

Alkanes Cyclic

group

Alkenes Alkynes

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Representation of Compounds


Molecular formula

Structural formula

exact ratio of the atoms in a molecule is given

C6H12O6 C10H22

shows the arrangement of atoms and bonds in a molecule

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Condensed structural formula

Bond-line formula

shows only specific bonds, other bonds are left out but implied

C are represented as point or corners

C-H bonds are left out but implied

Representation of Compounds

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Counting in Organic Chemistry


01 = meth-

02 = eth-

03 = prop-

04 = but-

05 = pent-

06 = hex-

07 = hept-

08 = oct-

09 = non-

10 = dec-

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Alkanes


Simplest type of organic compoundSaturated hydrocarbons

General formula: CnH2n+2

Name

MethaneEthane

Propane

Butane

Pentane

Hexane

Heptane

Octane

Nonane

Decane

# of C

12

3

4

5

6

7

8

9

10

MF

CH4C2H6C3H8C4H10C5H12C6H14

C7H16C8H18C9H20C10H22

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Alkanes


NameStructuralformula

Condensed

structural

formula

Bond-linestructure

Methane

Ethane

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Alkanes



Condensed

structural

formula

Bond-linestructure

Propane

Butane

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Alkanes



Condensed

structural

formula

Bond-linestructure

Pentane

Hexane

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Structural Isomers


molecules that have the same molecular formula but different structures

C4H

10 C4H10

primary (1) carbon- C directly bonded to only one other C

secondary (2) carbon- C directly bonded to two other C

tertiary (3) carbon- C directly bonded to three other C

NOTE:

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Nomenclature


PREFIX PARENT SUFFIX

The General Format

Substituents

name

location

Longestcontinuous

C-chain

-name ending

Halogens

-F, -Cl, -Br, -I

Alkyl groups

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Alkyl Groups


derived from simple alkanes that has lost 1 H atom

Methane Methyl Ethane Ethyl

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IUPAC rules


1. Determine longest continuous chain (i.e. parent hydrocarbon)

2

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IUPAC rules


2. Cite the name of substituent before the name of the parenthydrocarbon along with the number of the carbon to which it isattached.

2

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IUPAC rules


3. Number in the direction that gives the lower number for thelowest-numbered substituent. Substituents are listed inalphabetical order neglecting prefixes such as di- tri- tert-etc.

2

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IUPAC rules


4. When both directions yield the same lower number for thelowest numbered substituent, select the direction that yieldsthe lower number for the next lowest numbered substituent.

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IUPAC rules


5. If same substituent numbers are obtained in either direction,number in direction giving lowest number to the first namedsubstituent.

6. If compound has two or more chains of the same length,parent hydrocarbon is chain with greatest number ofsubstituents.

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IUPAC rules


7.Names such as sec-butyl and tert-butyl are acceptable, butsystematic substituent names are preferable.Numbering of the substituent begins with the carbon attached tothe parent hydrocarbon.This number together with the substituent name is placed inside

parentheses.

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Cycloalkanes


alkanes in ring structures

usually drawn using bondline structure

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Nomenclature of Cycloalkanes


1. Ring is the parent hydrocarbon unless the alkyl substituent hasmore carbons; in that case the substituent becomes the parenthydrocarbon.

If only one substituent, no need to give it a number.

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2. If the ring has 2 substituents, list in alphabetical order and givenumber 1 to first named group

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3. If there is more than one substituent, list in alphabetical order;one substituent is given the position number 1; number eitherclockwise or counterclockwise - lowest numbers

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Exercises


A

B

C

D EMSAESMALLA

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Answers to Exercises


A

B

C

D

E

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Exercises


A

B

C

D

E

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Answers to Exercises


BA C

D E

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Alkenes & Alkynes


Unsaturated hydrocarbon

Presence of double bond (alkene) and triple bond (alkyne)

General formula: alkene = CnH2n; alkyne = CnH2n-2

Name ends with ene (alkene); -yne(alkyne)

AlkeneEthene

Propene

Butene

Pentene

Hexene

HepteneOctene

Nonene

Decene

# of C2

3

4

5

6

78

9

10

MFC2H4C3H6C4H8C5H10C6H12

C7H14C8H16C9H18C10H20

AlkyneEthyne

Propyne

Butyne

Pentyne

Hexyne

HeptyneOctyne

Nonyne

Decyne

MFC2H2C3H4C4H6C5H8C6H10

C7H12C8H14C9H16C10H18

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Alkenes & Alkynes


1-propene 1-butene 2-butene

1-pentene 2-pentene

=

1-propyne

1-butyne 2-butyneMSAESMALLA

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Alkenes & Alkynes


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Alkyl Halide


common name: name of alkyl group + name of halogen, end with -ide

IUPAC name: treat the halogen as a substituent

methyl chloride ethyl fluoride

isopropyl iodide sec-butyl bromide

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Alkyl Halide


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Aromatics


refer to benzene and its structural derivatives

a cyclic conjugated molecule

planar and has a shape of a regular hexagon

all C are sp2-hybridized

Benzene

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Aromatics


Monosubstituted

Common name of monosubstituted benzene ring

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Aromatics


Disubstituted

1,2- 1,3- 1,4-

o-

(ortho-)

m- p-

(meta-) (para-)

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Functional Groups


hydrocarbon derivatives

structural features that classify compounds by reactivity

causes characteristic chemical behavior

determines physical properties

basis for naming organic compounds

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Alcohols


General Formula:

Nomenclature

common:

IUPAC:

R-OH

Name of parent alkyl, followed by alcohol

Name of parent as alkane, replace e with -ol

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Alcohols


1 alcohol 2 alcohol 3 alcohol

1 2 3

Classification

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Alcohols


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Ethers


General Formula:

Nomenclature

common:

IUPAC:

R-O-R

Name of 2 alkyl groups in alphabetical order,followed by ether

Name of shorter R group as alkyl, replace yl

with oxy then name of the longer R as alkane

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Aldehydes


General Formula:

Nomenclature

IUPAC: Name of parent as alkane, replace e with -al

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Ketone


General Formula:

Nomenclature

IUPAC: Name of parent as alkane, replace e with -one

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Carboxylic Acid


General Formula:

Nomenclature

IUPAC: Name of parent as alkane, replace e with oic+ acid

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Esters


General Formula:

Nomenclature

IUPAC: Name of alkyl, name of parent alkane replace e with oate

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Acid Halide


General Formula:

Nomenclature

IUPAC: Name of parent alkane replace e with oyl+ name of halogen as halide

, where X is a halogen (F, Cl, Br, I)

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Acid Anhydride


General Formula:

Nomenclature

IUPAC: Name of parent alkane replace e with oic+ anhydride

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Organic Nitrogen Compounds


General Formula:

Nomenclature: name ending is -amine

Amine

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General Formula:

Nomenclature: name ending is -amide

Amide

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General Formula:

Nomenclature: name ending is nitrile (or cyanide)

Nitrileor

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Organic Sulfur Compounds


General Formula:

Nomenclature: name ending is thiol

Thiol

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Summary

Functional group General formula Suffix Example

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organic nomenclature 2010

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